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358002

Sigma-Aldrich

(3aR)-(+)-Sclareolide

97%

Synonym(s):

(+)-Norambreinolide

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About This Item

Empirical Formula (Hill Notation):
C16H26O2
CAS Number:
564-20-5
Molecular Weight:
250.38
EC Number:
209-269-0
MDL number:
MFCD00134168
UNSPSC Code:
12352005
PubChem Substance ID:
24861957
NACRES:
NA.22

Assay

97%

form

powder

optical activity

[α]20/D +47°, c = 2% in chloroform

mp

124-126 °C (lit.)

SMILES string

[H][C@@]12CC[C@@]3(C)OC(=O)C[C@]3([H])[C@@]1(C)CCCC2(C)C

InChI

1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1

InChI key

IMKJGXCIJJXALX-SHUKQUCYSA-N

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General description

Sclareolide is a diterpenoid compound mainly used in the perfume industry for its amber like odor.

Application

(3aR)-(+)-Sclareolide may be used in the total syntheses of bioactive compounds such as (+)-chloropuupehenone, (+)-chloropuupehenol, cyslabdan, acuminolide and 17-O-acetylacuminolide. It may also be used in the preparation of γ-bicyclohomofarnesal, an ambergris odorant.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Superacid cyclization of homo-and bishomoisoprenoid acids.
Vlad PF, et al.
Chemistry of Heterocyclic Compounds, 27(3), 246-249 (1991)
Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide.
Zoretic PA, et al.
The Journal of Organic Chemistry, 63(4), 1156-1161 (1998)
Synthesis and Structural Revision of Cyslabdan.
Ohtawa M, et al.
Chemical & Pharmaceutical Bulletin, 64(9), 1370-1377 (2016)
Natural sesquiterpenoids.
Fraga BM.
Natural Product Reports, 20(4), 392-413 (2003)
Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities.
Hua DH, et al.
The Journal of Organic Chemistry, 69(18), 6065-6078 (2004)

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